Events
It's not just another day in paradise! You'll find doings and happenings up and down the Keys, nearly every day of the year. Check out the latest fun and frolic below.
Only-In-The-Keys Festivals & Events
There’s always something happening in the Florida Keys & Key West, from eclectic festivals focusing on the area’s colorful history, arts and notable cuisine to events that celebrate the Keys’ unique environment, underwater adventures and quirky ambiance.
See Some Shenanigans
Mile 0 Fest (2026)
Experience Mile 0 Fest in the stunning Florida Keys! Enjoy five days of top Texas Red Dirt & Americana music, beachfront parties, and unforgettable...
The Doo Wop Project at Tennessee Williams Theater
Featuring stars from the Broadway shows Jersey Boys, Motown, Beautiful and Hairspray, Doo Wop Project is inspired by inner city African American vocal...
St. Paddy's Island 5K/10K
We're so excited to bring you a fun 5K and 10K to our favorite and most popular place in Islamorada. St. Paddy's is a celebrated holiday throughout...
RAMS HEAD PRESENTS: MARTIN SEXTON LIVE WIDE OPEN TOUR 2026 at Key West Theater
Experience an unforgettable night in the Florida Keys! Catch acclaimed singer-songwriter Martin Sexton live at the Key West Theater on March 13, 2026...
John Frinzi & Aaron Scherz at Key West Theater
Experience John Frinzi & Aaron Scherz at Key West Theater (Mar 13, 2026) — an island-style evening of sun-soaked folk-pop, multi‑platinum songwriting...
The Original Marathon Seafood Festival (2026)
Experience the vibrant flavors of the Florida Keys at the Marathon Seafood Festival! Enjoy fresh local seafood, live music, arts & crafts, and family...
South Florida Symphony Orchestra: Dvořák’s Eighth & Sibelius’ Violin Concerto
Experience a season finale in Key West: South Florida Symphony Orchestra at Tennessee Williams Theatre on March 14, 2026, 7:30 PM. Maestra Sebrina...
Kim Gordon’s Black and Red Masquerade Ball at Key West Theater
Escape to the Key West Theater on March 14, 2026 for Kim Gordon’s Black & Red Masquerade Ball, a glamorous Venetian-style night of swing, jazz, blues...
Golden Girls: The Tribute Show - A Drag Parody at Key West Theater
Join GOLDEN GIRLS: THE TRIBUTE SHOW in Key West — a hilarious drag parody of Dorothy, Rose, Blanche & Sophia with live scenes, musical numbers...
Hilariously Inappropriate Drag Queen Bingo: A Comedy Show with Balls at Key West Theater
Hilariously Inappropriate Drag Queen Bingo — A Comedy Show with Balls comes to Key West on March 15, 2026. Two hours of raunchy, ridiculous fun...
Carr-Petrova Duo - Impromptu Classical Concerts at Tennessee Williams Theater
\- Impromptu Classical Concerts - Described as "ravishing" (Strad), "enlightened" (BBC), "explosive" (Virginia Gazette), and "irresistibly elegant"...
Library Speaker Series: Christopher Castellani
Join acclaimed novelist Christopher Castellani for an intimate Speaker Series talk at Key West Library on March 16, 2026, 6:00 PM. Free admission —...
Larry Joe Taylor & Guest at Key West Theater
Experience Larry Joe Taylor’s soulful Coastal & Western sound live at Key West Theater on March 19, 2026. Bring island-time vibes, sing along to...
The Italian American Dream with Analisa and John
Experience "The Italian American Dream" with Analisa & John Gallo in Key West on Mar 19. Dinner at 5:30pm, show 6:45pm; $50 includes dinner and a...
Key West International Dance Company - 'MURDER OR MUTINY?'
This new show, set in the early 1800's, traces Captain Samuel's precarious voyages as a sea trader in the days of the spice route. While running opium...